Dibenz[a,h]anthracene

• Formula: C₂₂H₁₄
• Molecular weight: 278.3466
• IUPAC Standard InChI: InChI=1S/C22H14/c1-3-7-19-15(5-1)9-11-17-14-22-18(13-21(17)19)12-10-16-6-2-4-8-20(16)22/h1-14H Copy

  
• IUPAC Standard InChIKey: LHRCREOYAASXPZ-UHFFFAOYSA-N Copy
• CAS Registry Number: 53-70-3
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Isotopologues:
  • dibenzo[a,h]anthracene-d14
• Other names: Dibenzo[a,h]anthracene; DBA; 1,2:5,6-Benzanthracene; 1,2:5,6-Dibenzanthracene; 1,2:5,6-Dibenzoanthracene; 1,2,5,6-Dibenzanthracene; DB(a,h)A; Dibenz(a,h)antracene; 1,2,5,6-Dibenzanthraceen; 1,2:5,6-Dibenz(a)anthracene; 1,2,5,6-DBA; Rcra waste number U063; NSC 22433
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
• Data at other public NIST sites:
  • NIST Polycyclic Aromatic Hydrocarbon Structure Index
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Gas phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Condensed phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Donald R. Burgess, Jr.

Phase change data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Enthalpy of vaporization

Enthalpy of sublimation

Enthalpy of fusion

Gas phase ion energetics data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data evaluated as indicated in comments:
L - Sharon G. Lias

Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess

Electron affinity determinations

Ionization energy determinations

IR Spectrum

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Coblentz Society, Inc.

Condensed Phase Spectrum

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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.

Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

Gas Chromatography

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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Lee's RI, non-polar column, isothermal

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Lee's RI, non-polar column, temperature ramp

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Lee's RI, non-polar column, custom temperature program

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Roux, Temprado, et al., 2008
Roux, M.V.; Temprado, M.; Chickos, J.S.; Nagano, Y., Critically Evaluated Thermochemical Properties of Polycyclic Aromatic Hydrocarbons, J. Phys. Chem. Ref. Data, 2008, 37, 4, 1855-1996. [all data]

Dorofeeva O.V., 1988
Dorofeeva O.V., Thermodynamic Properties of Polycyclic Aromatic Hydrocarbons in the Gaseous Phase. Institute for High Temperatures, USSR Academy of Sciences, Preprint No.1-238 (in Russian), Moscow, 1988. [all data]

Dorofeeva O.V., 1986
Dorofeeva O.V., On calculation of thermodynamic properties of polycyclic aromatic hydrocarbons, Thermochim. Acta, 1986, 102, 59-66. [all data]

Moiseeva N.F., 1989
Moiseeva N.F., Development of Benson group additivity method for estimation of ideal gas thermodynamic properties of polycyclic aromatic hydrocarbons, Thermochim. Acta, 1989, 153, 77-85. [all data]

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Frenkel M., Thermodynamics of Organic Compounds in the Gas State, Vol. I, II, Thermodynamics Research Center, College Station, Texas, 1994, 1994. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Casellato, Vecchi, et al., 1973
Casellato, F.; Vecchi, C.; Girell, A., Differential calorimetric study of polycyclic aromatic hydrocarbons, Thermochim. Acta, 1973, 6, 4, 361, https://doi.org/10.1016/0040-6031(73)87003-0 . [all data]

Wakayama and Inokuchi, 1967
Wakayama, N.; Inokuchi, H., Heats of Sublimation of Polycyclic Aromatic Hydrocarbons and Their Molecular Packings, Bull. Chem. Soc. Jpn., 1967, 40, 2267-71. [all data]

Schuyer, Blom, et al., 1953
Schuyer, J.; Blom, L.; Van Krevelen, D.W., Molar refraction of condensed aromatic compounds., Trans. Faraday Soc., 1953, 49, 1391. [all data]

Jones and Neuworth, 1944
Jones, R.C.; Neuworth, M.B., The Ultraviolet Absorption Spectra of Hydrocarbon-Trinitrobenzene Complexes, J. Am. Chem. Soc., 1944, 66, 1497. [all data]

Krishnan and Banerjee, 1935
Krishnan, K.S.; Banerjee, S., An Orthorhombic Crystalline Modification of 1,2,5,6-Dibenzanthracene, Z. Kristallogr., Kristallgeom., Kristallphys., Kristallchem., 1935, 91, 170. [all data]

Hanshaw, Nutt, et al., 2008
Hanshaw, William; Nutt, Marjorie; Chickos, James S., Hypothetical Thermodynamic Properties. Subcooled Vaporization Enthalpies and Vapor Pressures of Polyaromatic Hydrocarbons, J. Chem. Eng. Data, 2008, 53, 8, 1903-1913, https://doi.org/10.1021/je800300x . [all data]

Kruif, 1980
Kruif, C.G., Enthalpies of sublimation and vapour pressures of 11 polycyclic hydrocarbons, J. Chem. Thermodyn., 1980, 12, 243-248. [all data]

Wakayama and Inokuchi, 1967, 2
Wakayama, N.; Inokuchi, H., Heats of sublimation of polycyclic aromatic hydrocarbons and their molecular packings, Bull. Chem. Soc. Jpn., 1967, 40, 2267. [all data]

Lei, Chankalal, et al., 2002
Lei, Ying Duan; Chankalal, Raymond; Chan, Anita; Wania, Frank, Supercooled Liquid Vapor Pressures of the Polycyclic Aromatic Hydrocarbons, J. Chem. Eng. Data, 2002, 47, 4, 801-806, https://doi.org/10.1021/je0155148 . [all data]

Wakayama and Inokuchi, 1967, 3
Wakayama, Nobuko; Inokuchi, Hiroo, Heats of Sublimation of Polycyclic Aromatic Hydrocarbons and Their Molecular Packings, Bull. Chem. Soc. Jpn., 1967, 40, 10, 2267-2271, https://doi.org/10.1246/bcsj.40.2267 . [all data]

Kestens, Auclair, et al., 2010
Kestens, Vikram; Auclair, Guy; Drozdzewska, Katarzyna; Held, Andrea; Roebben, Gert; Linsinger, Thomas, Thermodynamic property values of selected polycyclic aromatic hydrocarbons measured by differential scanning calorimetry, J Therm Anal Calorim, 2010, 99, 1, 245-261, https://doi.org/10.1007/s10973-009-0440-6 . [all data]

Acree, 1991
Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [all data]

Becker and Chen, 1966
Becker, R.S.; Chen, E., Extension of Electron Affinities and Ionization Potentials of Aromatic Hydrocarbons, J. Chem. Phys., 1966, 45, 7, 2403, https://doi.org/10.1063/1.1727954 . [all data]

Schmidt, 1977
Schmidt, W., Photoelectron spectra of polynuclear aromatics. V. Correlations with ultraviolet absorption spectra in the catacondensed series, J. Chem. Phys., 1977, 66, 828. [all data]

Gallegos, 1968
Gallegos, E.J., Mass spectrometry and ionization energies of some condensed-ring aromatic and heterocyclic compounds, J. Phys. Chem., 1968, 72, 3452. [all data]

Kuroda, 1964
Kuroda, H., Ionization potentials of polycyclic aromatic hydrocarbons, Nature, 1964, 201, 1214. [all data]

Briegleb, 1964
Briegleb, G., Electron affinity of organic molecules, Angew. Chem. Intern. Ed., 1964, 3, 617. [all data]

Birks and Stifkin, 1961
Birks, J.B.; Stifkin, M.A., π-Electronic excitation and ionization energies of condensed ring aromatic hydrocarbons, Nature, 1961, 191, 761. [all data]

Matsen, 1956
Matsen, F.A., Electron affinities, methyl affinities, and ionization energies of condensed ring aromatic hydrocarbons, J. Chem. Phys., 1956, 24, 602. [all data]

Clar and Schmidt, 1976
Clar, E.; Schmidt, W., Correlations between photoelectron and phosphorescence spectra of polycyclic hydrocarbons, Tetrahedron, 1976, 32, 2563. [all data]

Clar and Schmidt, 1975
Clar, E.; Schmidt, W., Correlations btween photoelectron and ultraviolet absorption spectra of polycyclic hydrocarbons and the number of aromatic sextets, Tetrahedron, 1975, 31, 2263. [all data]

Boschi, Clar, et al., 1974
Boschi, R.; Clar, E.; Schmidt, W., Photoelectron spectra of polynuclear aromatics. III. The effect of nonplanarity in sterically overcrowded aromatic hydrocarbons, J. Chem. Phys., 1974, 60, 4406. [all data]

Rudenko, Bulychova, et al., 1984
Rudenko, B.A.; Bulychova, Z.Yu.; Topunov, V.N.; Itsikson, L.B., Regularities in changes of retention indices for polycyclic aromatic hydrocarbons depending on their structure and polarity of stationary phase, Zh. Anal. Khim., 1984, 39, 4, 700-706. [all data]

Grimmer and Böhnke, 1976
Grimmer, G.; Böhnke, H., Anreicherung und gas-chromatographische Profil-Analyse der polycyclischen aromatischen Kohlenwasserstoffe in Schmieröl, Chromatographia, 1976, 9, 1, 30-40, https://doi.org/10.1007/BF02270595 . [all data]

Grimmer and Böhnke, 1975
Grimmer, G.; Böhnke, H., Polycyclic aromatic hydrocarbon profile analysis of high-protein foods, oils, and fats by gas chromatography, J. Ass. Offic. Anal. Chem, 1975, 58, 4, 725-733. [all data]

Grimmer and Böhnke, 1972
Grimmer, G.; Böhnke, H., Bestimmung des Gesamtgehaltes aller polycyclischen aromatischen Kohlenwasserstoffe in Luftstaub und Kraftfahrzeugabgas mit der Capillar-Gas-Chromatographie, Z. Anal. Chem., 1972, 261, 4-5, 310-314, https://doi.org/10.1007/BF00786987 . [all data]

Beernaert, 1979
Beernaert, H., Gas Chromatographic Analysis of Polyclylic Aromatic Hydrocarbons, J. Chromatogr., 1979, 173, 1, 109-118, https://doi.org/10.1016/S0021-9673(01)80450-7 . [all data]

Carugno and Rossi, 1967
Carugno, N.; Rossi, S., Evaluation of polynuclear hydrocarbons in cigarette smoke by glass capillary columns, J. Gas Chromatogr., 1967, 5, 2, 103-106, https://doi.org/10.1093/chromsci/5.2.103 . [all data]

Oda, Ichikawa, et al., 1996
Oda, J.; Ichikawa, S.; Mori, T., Analysis of polycyclic aromatic hydrocarbons in airborne particulates by capillary GC/MS method with programmed temperature relative retention index, Bunseki Kagaku, 1996, 45, 9, 825-835, https://doi.org/10.2116/bunsekikagaku.45.825 . [all data]

Dumitrescu, Buda, et al., 2000
Dumitrescu, V.; Buda, W.; Medvedovici, A., Evaluation of new stationary phases for capillary gas chromatography, Rev. Roum. Chim., 2000, 45, 4, 313-318. [all data]

Oda, Yasuhara, et al., 1998
Oda, J.; Yasuhara, A.; Matsunaga, K.; Saito, Y., Identification of polycyclic aromatic hydrocarbons of the particulate accumulated in the tunnel duct of freeway and generation of their oxygenated derivatives, Jpn. J. Toxicol. Environ. Health, 1998, 44, 5, 334-351, https://doi.org/10.1248/jhs1956.44.334 . [all data]

Kaliszan and Lamparczyk, 1978
Kaliszan, R.; Lamparczyk, H., A Relationship between the Connectivity Indices and Retention Indices of Polycyclic Aromatic Hydrocarbons, J. Chromatogr. Sci., 1978, 16, 6, 246-248, https://doi.org/10.1093/chromsci/16.6.246 . [all data]

Shlyakhov, 1984
Shlyakhov, A.F., Gas chromatography in organic geochemistry, Nedra, Moscow, 1984, 221. [all data]

Skrbic and Onjia, 2006
Skrbic, B.; Onjia, A., Prediction of Lee Retention Indices of Polycyclic Aromatic Hydrocarbons by Artificial Neural Networks, J. Chromatorg. A, 2006, 1108, 2, 279-284, https://doi.org/10.1016/j.chroma.2006.01.080 . [all data]

Pedersen, Durant, et al., 2005
Pedersen, D.U.; Durant, J.L.; Taghizadeh, K.; Hemond, H.F.; Lafleur, A.L.; Cass, G.R., Human cell mutagenes in respirable airborne particles from the Northeastern United States. 2. Quantification of mutagenes and other organic compounds., Environ. Sci. Technol., 2005, 39, 24, 9547-9560, https://doi.org/10.1021/es050886c . [all data]

Marynowski, Pieta, et al., 2004
Marynowski, L.; Pieta, M.; Janeczek, J., Composition and source of polycyclic aromatic compounds in deposited dust from selected sites around the Upper Silesia, Poland, Geol. Q., 2004, 48, 2, 169-180. [all data]

Chen, Keeran, et al., 2002
Chen, P.H.; Keeran, W.S.; Van Ausdale, W.A.; Schindler, D.R.; Roberts, D.W., Application of Lee retention indices to the confirmation of tentatively identified compounds from GC/MS analysis of environmental samples, Technical paper, Analytical Services Division, Environmental ScienceEngineering, Inc, PO Box 1703, Gainesville, FL 32602, 2002, 11. [all data]

Wang, Jia, et al., 2000
Wang, J.; Jia, C.R.; Wong, C.K.; Wong, P.K., Characterization of polycyclic aromatic hydrocarbons created in lubricating oils, Water Air Soil Poll., 2000, 120, 3/4, 381-396, https://doi.org/10.1023/A:1005251618062 . [all data]

Piao, Chu, et al., 1999
Piao, M.; Chu, S.; Zheng, M.; Xu, X., Characterization of the combustion products of polyethylene, Chemosphere, 1999, 39, 9, 1497-1512, https://doi.org/10.1016/S0045-6535(99)00054-5 . [all data]

Shaogang and Xiaobai, 1994
Shaogang, C.; Xiaobai, X., System for calculating the linear temperature-programmed retention indices of polycylic aromatic compounds, J. Hi. Res. Chromatogr., 1994, 17, 5, 339-342, https://doi.org/10.1002/jhrc.1240170511 . [all data]

Donnelly, Abdel-Hamid, et al., 1993
Donnelly, J.R.; Abdel-Hamid, M.S.; Jeter, J.L.; Gurka, D.F., Application of gas chromatographic retention properties to the identification of environmental contaminants, J. Chromatogr., 1993, 642, 1-2, 409-415, https://doi.org/10.1016/0021-9673(93)80106-I . [all data]

Guillén, Blanco, et al., 1989
Guillén, M.D.; Blanco, J.; Bermejo, J.; Blanco, C.G., Temperature programmed retention indices of some PAHs on Capillary columns coated with OV-1701 and SE-54, J. Hi. Res. Chromatogr., 1989, 12, 8, 552-554, https://doi.org/10.1002/jhrc.1240120816 . [all data]

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Wise, S.A.; Benner, B.A.; Byrd, G.D.; Chesler, S.N.; Rebbert, R.E.; Schantz, M.M., Determination of polycyclic aromatic hydrocarbons in a coal tar standard reference material, Anal. Chem., 1988, 60, 9, 887-894, https://doi.org/10.1021/ac00160a012 . [all data]

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Vassilaros, D.L.; Kong, R.C.; Later, D.W.; Lee, M.L., Linear retention index system for polycyclic aromatic compounds. Critical evaluation and additional indices, J. Chromatogr., 1982, 252, 1-20, https://doi.org/10.1016/S0021-9673(01)88394-1 . [all data]

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Wang, Z.; Li, K.; Lambert, P.; Yang, C., Identification, characterization and quantitation of pyrogenic polycylic aromatic hydrocarbons and other organic compounds in tire fire products, J. Chromatogr. A, 2007, 1139, 1, 14-26, https://doi.org/10.1016/j.chroma.2006.10.085 . [all data]

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Sremac, S.; Skrbic, B.; Onjia, A., Artificial neural network prediction of quantitative structure-retention relationships of polycyclic aromatic hydrocarbons in gas chromatography, J. Serb. Chem. Soc., 2005, 70, 11, 1291-1300, https://doi.org/10.2298/JSC0511291S . [all data]

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Ré-Poppi, N.; Santiago-Silva, M.R., Identification of polycyclic aromatic hydrocarbons and methoxylated phenols in wood smoke emitted during production of charcoal, Chromatographia, 2002, 55, 7/8, 475-481, https://doi.org/10.1007/BF02492280 . [all data]

Guillen, Iglesias, et al., 1992
Guillen, M.D.; Iglesias, M.J.; Dominguez, A.; Blanco, C.G., Polynuclear aromatic hydrocarbon retention indices on SE-54 stationary phase of the volatile components of a coal tar pitch. Relationships between chromatographic retention and thermal reactivity, J. Chromatogr., 1992, 591, 1-2, 287-295, https://doi.org/10.1016/0021-9673(92)80246-Q . [all data]

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Takada, H.; Onda, T.; Ogura, N., Determination of polycyclic aromatic hydrocarbons in urban street dusts and their source materials by capillary gas chromatography, Environ. Sci. Technol., 1990, 24, 8, 1179-1186, https://doi.org/10.1021/es00078a005 . [all data]

Naikwadi, Charbonneau, et al., 1987
Naikwadi, K.P.; Charbonneau, G.M.; Karasek, F.W.; Clement, R.E., Separation and Identification of Organic Compounds in Air Particulate Extracts by High-Performance Liquid Chromatography and Gas Chromatography-Mass Spectrometry, J. Chromatogr., 1987, 398, 227-237, https://doi.org/10.1016/S0021-9673(01)96508-2 . [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, References

• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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